Common fears with content-level transparency
6 min read

Common fears with content-level transparency

I know it also sounds hard and scary to think about making all of the information produced at your company available to anyone at any time. And I said I'd share more about this soon and here we are.

You are not alone in your fears about upsetting or distracting your employees. Being considerate about this kind of thing is part of what makes you a good leader and a good friend. But, with a good system in place, you can unlock unprecedented trust and connection at your company.

So with that, here are the most common fears I hear about, and some stories to accompany them.

True stories of Brie’s early experiences with Stripe’s email transparency system.

The fear of the entire company as your audience

I was having a really busy day when a request came in that required another Stripe’s input. Old email habits led me to consider forwarding that email to my colleague without any information. This kind of behavior saves me some time, but requires my teammate on the other side to do some digging into the email to figure out how to action it.

As I went to cc the open email list on my rotely-forwarded email, I thought about what my manager, new colleagues, or maybe even Stripe’s founders would think if they saw this email coming from me. I didn’t like the idea of someone thinking to themselves “Brie protects her time at the expense of someone else’s.” So, I took the extra 60 seconds to add the required context in the body of my forwarded email. When I think about it, I bet it saved my colleague more than 60 seconds. It was a small, but still global, optimization.

The fear of colleagues lurking on your work, part 1

In my second week on the job as Stripe second-ever account manager, I got a question from a user I wasn’t quite sure how to answer. Like a good Stripe, I looked through our docs (internal and external) and, when that failed to turn anything up, referred to the email archives to see if anyone else had answered this question for another user. Voila! Relieved I didn’t have to ask my busy colleague for help, proud of myself for solving my own problem, and impressed with the effectiveness of this email transparency thing, I copied my colleague’s response, pasted it into my email, bcc’d the appropriate email list, and hit send.

Within minutes, a colleague who worked on a different team in a different part of the organization replied to me explaining this wasn’t quite how things worked. A better response to the user would have been x (he wrote it in a way that would allow me to copy-paste into my next email).

I got that sinking feeling that I messed up. I was sure my colleague thought I was a dummy, that I was bad at my job, and I’d probably get fired soon. In a moment of panic, I thought about forwarding my colleagues original email and showing him that it wasn’t me who got it wrong but I stopped myself.

I sent the user a second clarifying email (bcc’ing my colleague because I used his words) and then pinged him to thank him for the feedback. He responded immediately and said (paraphrased) “not your fault at all! we need to do a better job documenting these kinds of changes! That update was made last week and I don’t think anyone told the account managers. We’re not quite used to having account managers here yet.” I felt immediately not only relieved about my performance, but also like my colleague was on my side and wanted to help solve problems with me (not point fingers at me).

It was also the start to a great working relationship with this colleague because in this teeny, tiny interaction, it was quickly established that we were colleagues that could exchange feedback and care.

The fear of colleagues lurking on your work, part 2

To do a good job as an Account Manager supporting many of Stripe’s largest users, I had to ramp up on a lot of product and industry knowledge. Payments, Stripe’s API, and these particular user integrations were very complex and relied on many deeply technical details. So, I started keeping a log of things I learned in a document called “what Brie learned today.” I made the doc public to the company by default.

One of Stripe’s earliest and most impactful employees stumbled across the document. He posted into a public channel and said (paraphrased) “awesome idea from Brie to keep track of what she’s learning. This can also be a resource for us to consider what’s counterintuitive or hard about how things work.” Then, lots of other Stripes piled on to say nice things and thank me for keeping such diligent notes. That was a nice moment. And I didn’t have to do any icky “managing up” to get it.

The fear of colleagues lurking on your work, part 3

I diligently published notes from my meeting into the company with the subject line “postmortem: $workstream_name.” One of the new company leaders pinged soon after. “Thanks for sending those notes; really interesting. Reminder to use the term retrospective instead of postmortem, though. Postmortem is a little morbid.”

After I got over the initial tingles of “ugh, I did something wrong,” I thought, “wow, this new leader really gets and cares about the culture here. And, he’s really paying attention to the details of what’s going on at our company. How awesome is that.” I said “oops, thanks for the reminder!” and went about my day.

This leader and I bumped into each other in the kitchen on Halloween a few months later and joked that the skull decor was “a little morbid.” That interaction felt a lot more authentic and meaningful than an exchange about the weather.


The fear of a complete and detailed record of your work for all to see


My manager asked me to meet her in a conference room at my next free moment. GULP.

One of my clients had emailed her saying that they wanted their account manager (me) replaced. She said that I was unresponsive to her requests and that I wasn’t able to navigate the complexities of her integration. I was really frustrated to hear this report on my work, especially because I did not feel like it was an accurate representation of the status of our work together.

I prepared to start defending myself and my work to my manager, but before I could, she assured me that she had already looked through my interactions with this user and did not see any evidence of the user’s interpretation of our work together.  She cited the quick response times and clear communication directly from my emails. My manager went on to assure me that I was doing a great job and that she did not appreciate users misrepresenting my work through this escalation. She asked if I had any additional context I would like to provide to help prepare her for the conversation she was going to have directly with the user.

I felt deeply, deeply cared for and paid attention to in this moment. And, I think everyone was relieved we didn’t have to engage in any kind of he-said-she-said to get to the bottom of what was happening.

True fears I hear company leaders articulate

The fear of upsetting employees

Every leader gets that “I’m worried new-employee Sam will get spooked if I mention this thing that disappointed me during their very first All Hands,” pang. (This kind of thinking works for your non-work relationships so you’re well trained on it). That’s a good time to remind yourself that you hired Sam not only because they’re a great accountant, but also because they’re a bright, thoughtful, mature team member that can be trusted to understand the nuance and consider the overall health and ambition of the company when they hear your critical evaluation of work. And, if you speak to a challenge with sufficient context and care when you do mention that thing at All Hands, they might even get inspired to help play a role in solving it.


The fear of distracting employees

Every leader gets that knee-jerk “no need to share this with Alex in Marketing just yet” instinct. That’s a good time to remind yourself that your best employees aren’t nosy or lacking trust in their teammates. They’re inquisitive and context-seeking because they want to do what’s best for the whole company, not just themselves or their team.


The fear of the information firehose

Every leader of an open-sourced-internally company (and even somewhat-open-sourced-internally companies) get feedback about the “information firehose around here!” You can remind yourself (and the person that gave you that feedback) that human brains are really, really good at parsing information and pattern matching across lots and lots of information. Plus, there are tons of tools and resources that help people manage their inboxes effectively. And lastly, that the benefits of sharing far outweigh the tradeoffs.